R. Nadano, J. Ichikawa
2006
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Journal
Synthesis
Abstract
Introduction of a 1-(trifluoromethyl)vinyl group has been accomplished by the reaction of thermally unstable 1-(trifluoromethyl)vinyllithium (1) with strained cyclic ethers. Treatment of 2-bromo-3.3.3-trifluoropropene with butyllithium generates 1. which in turn reacts with several oxiranes or an oxetane at -100 °C in the presence of BF 3 .OEt 2 to afford the corresponding 2-trifluoromethyl- -1-alkenes bearing a hydroxy group on the 4- or 5-position. An enantiopure oxirane undergoes ring-opening without racemization. providing an optically active homoallyllic alcohol with a 3-trifluoromethyl group.